"Show all" option enabled

You might want to check our site IXXX.com for a better experience.

Undo

Sissy Training (261,546)

Liam Jacobson Private Show

62% HD 2:00 / 11:34

Liam Jacobson Private Show

Flirt4Free 10 months ago

Sissy Panty Slut Sph JOI

Sissy Panty Slut Sph JOI

XHamster 4 months ago

Seus & Dairon & Jose Private Show

65% HD 2:00 / 7:28

Seus & Dairon & Jose Private Show

Flirt4Free 8 months ago

Wear These for Step-mommy!

Wear These for Step-mommy!

XHamster 2 years ago

Emily & Stesha Private Show

62% 4K 2:00 / 14:58

Emily & Stesha Private Show

Flirt4Free 8 months ago

Nix Paradise Private Show

HD 2:00 / 59:53

Nix Paradise Private Show

Flirt4Free 6 years ago

Fucked and on the Edge of Orgasm - Sissy Slut Training

65% HD 1:01 / 14:43

Fucked and on the Edge of Orgasm - Sissy Slut Training

FapHouse 1 year ago

can you make me cum ? - Part 2

47% HD 2:00 / 4:52

can you make me cum ? - Part 2

Flirt4Free 6 months ago

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

51% HD 0:39 / 12:50

Part 1 My Husband Turned Into Latex Sissy Doll Good to Fuck - Mistress Julia

FapHouse 1 year ago

Dimitry Rolex & Liliith Private Show

50% HD 2:00 / 23:20

Dimitry Rolex & Liliith Private Show

Camster 2 years ago

Paulo & Liam Private Show

58% HD 2:00 / 10:03

Paulo & Liam Private Show

Flirt4Free 2 months ago

It's Not Gay if Its a Bet Gay Bisexual Encouragement

It's Not Gay if Its a Bet Gay Bisexual Encouragement

XHamster 1 year ago

Rimjob for feminized husband in stocking

Rimjob for feminized husband in stocking

XHamster 3 years ago

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

Red Satin and Hot Cock Sucking and Masturbating with a Cloth at Step-auntie Lady Victoria Valente

XHamster 4 months ago

Dildo Dolly 2

56% HD 1:01 / 15:31

FapHouse 3 years ago

Ronnie Cranfort Private Show

48% HD 2:00 / 9:35

Ronnie Cranfort Private Show

Flirt4Free 3 years ago

submissive asian ladyboy slave training & anal fisting

submissive asian ladyboy slave training & anal fisting

PornBox 2 months ago

Jhanne Cherry Private Show

60% 4K 2:00 / 6:21

Jhanne Cherry Private Show

Flirt4Free 1 year ago

Electra Joness Private Show

66% HD 2:00 / 4:22

Electra Joness Private Show

Camster 3 days ago

Sissy Anal Needs

75% HD 1:01 / 11:39

Sissy Anal Needs

FapHouse 1 year ago

Deep Fisting Compilation Real Sissy Training

72% HD 1:01 / 9:52

Deep Fisting Compilation Real Sissy Training

FapHouse 2 years ago

Strap on fun and asshole licking

66% 1:01 / 14:14

Strap on fun and asshole licking

FapHouse 4 years ago

Anal Training 105

HD 1:01 / 43:37

Anal Training 105

FapHouse 2 months ago

Sissy training with Femdom Headmistress Tangent

Sissy training with Femdom Headmistress Tangent

BigTitsLust 3 weeks ago

Husband Turned Girlfriend Pt 5

54% HD 0:15 / 20:29

Husband Turned Girlfriend Pt 5

IWantClips 3 years ago

I'm not Gay but...

I'm not Gay but...

IWantClips 11 months ago

TS Carmen Masters Turns Hung Muscle Wang Into Her Personal Sissy male In Pink Underware & Heels

TS Carmen Masters Turns Hung Muscle Wang Into Her Personal Sissy male In Pink Underware & Heels

ShemaleSin 1 day ago

Blessed Japanese Fresh Yr-Crimson food contest and super-cute deep-throat job

Blessed Japanese Fresh Yr-Crimson food contest and super-cute deep-throat job

TrannyGem 4 years ago

Sissy Chastity Maid Service Training With Ria Bentley

Sissy Chastity Maid Service Training With Ria Bentley

XHamster 10 months ago

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

Shivering and Leaking of Lust and Frustration! - Chastity Training, Pantyhose Domination and Orgasm Denial with Miss Adrastea

XHamster 2 months ago

ANAL INSTRUCTING ASSGASM

ANAL INSTRUCTING ASSGASM

SortPorn 2 years ago

Paulo & Jose & Sander Private Show

50% HD 2:00 / 10:44

Paulo & Jose & Sander Private Show

Flirt4Free 3 months ago

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

Strict Stepmom Femdom Fuck: Deep Fisting, Deep Throat Training, Sissification, Pee, Dirty Talk! Arya Grander

BDSMX 8 months ago

Femdom Mastix Dominant-bitch V humiliates & fully feminizes chastity cuckold sissy sub thrall w/ sph 1/three

Femdom Mastix Dominant-bitch V humiliates & fully feminizes chastity cuckold sissy sub thrall w/ sph 1/three

SortPorn 2 years ago

Katharine Cane Party on Aug 29, 2026 - Part 2

4K 2:00 / 1:12:23

Katharine Cane Party on Aug 29, 2026 - Part 2

Flirt4Free 3 weeks ago

Zack Watson Private Show

55% 4K 2:00 / 8:56

Zack Watson Private Show

Flirt4Free 1 year ago

Sophia Loreen Private Show

65% 4K 2:00 / 10:47

Sophia Loreen Private Show

Camster 2 months ago

Slave training in heat

Slave training in heat

Lesbian8 1 year ago

i like extraordinary assfuck hookup cuming sounding transgender queer etero

i like extraordinary assfuck hookup cuming sounding transgender queer etero

Gayhub 3 days ago

Locktober Special - Day 14: Cleanig Day

Locktober Special - Day 14: Cleanig Day

Clips4sale 2 years ago

Sissification and Rope Bondage for Nosey Stepbrother

60% HD 1:01 / 27:02

Sissification and Rope Bondage for Nosey Stepbrother

FapHouse 2 years ago

Sissy Slut - Left in the park as fucktoy

Sissy Slut - Left in the park as fucktoy

XHamster 4 years ago

Does my hand fit in his little ass?

Does my hand fit in his little ass?

XHamster 1 year ago

Mistress Susi - the Straight Slaves First Sissy Blowjob

57% 1:01 / 9:10

Mistress Susi - the Straight Slaves First Sissy Blowjob

FapHouse 2 weeks ago

Anal Slut Ryan74 Inserts Cold Coca Cola Can in Ass

Anal Slut Ryan74 Inserts Cold Coca Cola Can in Ass

XHamster 1 year ago

rough triple anal ride for our little sissy

65% HD 0:30 / 12:27

rough triple anal ride for our little sissy

PornBox 1 month ago

Double Sissy Discipline

52% HD 1:01 / 12:34

Double Sissy Discipline

FapHouse 11 months ago

Innocent Boy Seduced Into Becoming a Cum Slut Slave for Life

HD 0:39 / 21:47

Innocent Boy Seduced Into Becoming a Cum Slut Slave for Life

FapHouse 2 months ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 2 days ago

Sissy takes its cage distant during riding a massive 16 vibrator and shags the nut beyond concerning its tiny clit.

Sissy takes its cage distant during riding a massive 16 vibrator and shags the nut beyond concerning its tiny clit.

WebcamBros 1 year ago

Jhanne Cherry Private Show

Jhanne Cherry Private Show

Camster 1 year ago

Femboy Cumdump Pushes out Gallons of Cum

Femboy Cumdump Pushes out Gallons of Cum

XHamster 2 years ago

Two Pathetic Sissies Have to Suck and Fuck Each Other

Two Pathetic Sissies Have to Suck and Fuck Each Other

XHamster 9 months ago

Christian Rey & Elvis & Stuard Private Show

41% HD 2:00 / 9:58

Christian Rey & Elvis & Stuard Private Show

Flirt4Free 2 years ago

Sissy Training - Teaching My Friend How to Give a Blowjob

60% HD 0:39 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

FapHouse 2 years ago

Female-dom Nika and her feminized doxy. The feminization of the guy. Thrall dance

Female-dom Nika and her feminized doxy. The feminization of the guy. Thrall dance

FreePorn8 1 year ago

Master Collins & Elvis Private Show

58% HD 2:00 / 4:26

Master Collins & Elvis Private Show

Flirt4Free 4 years ago

Christian Rey & Elvis & Stuard Private Show

63% HD 2:00 / 12:01

Christian Rey & Elvis & Stuard Private Show

Flirt4Free 2 years ago

My Favorite Black Dress

67% HD 2:00 / 4:22

My Favorite Black Dress

Flirt4Free 2 years ago

Step-stepmommy's -wmv

Step-stepmommy's -wmv

FapHouse 1 month ago

Crossdresser in High Heels Gets Anal Pussy Machine Fucked

Crossdresser in High Heels Gets Anal Pussy Machine Fucked

XHamster 1 year ago

Gooner JOI Pleather Mommy

Gooner JOI Pleather Mommy

Tranny.one 2 years ago

Mike Swift & David Golden Private Show

64% HD 2:00 / 11:21

Mike Swift & David Golden Private Show

Flirt4Free 2 months ago

Caged up and Lost the Key

Caged up and Lost the Key

XHamster 3 months ago

Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony

Pornstar Ria Bentley Takes Giant BBC On Public Hotel Balcony

XHamster 1 year ago

scum Instructing jizz guzzling 2

scum Instructing jizz guzzling 2

TransTube.tv 1 year ago

Put this on for me now, my slut! - Sissy Training and Pantyhose Domination with Miss Adrastea

HD 0:10 / 12:14

Put this on for me now, my slut! - Sissy Training and Pantyhose Domination with Miss Adrastea

LoyalFans 2 months ago

Heather: Femme Tour

Heather: Femme Tour

4Gay 2 years ago

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

78% HD 1:01 / 7:58

Stepsister Fuck Stepbrother in Ass Very Big Strap on Dildo Vibrator Anal Pegging Femdom Spanking

FapHouse 1 year ago

Trans Girl Tied and Teased

67% HD 0:39 / 13:07

Trans Girl Tied and Teased

FapHouse 2 years ago

The Sissy Wedding - Brides share their first suck

Premium 4K 10:23

The Sissy Wedding - Brides share their first suck

Clips4sale 4 days ago

Riding And In 4 Part 3

HD 0:39 / 12:18

Riding And In 4 Part 3

FapHouse 1 year ago

sexy trans slut HUGE ANAL GAPE cums HANDS FREE

63% HD 0:17 / 8:03

sexy trans slut HUGE ANAL GAPE cums HANDS FREE

Clips4sale 4 weeks ago

Sissy POV - Sucking huge white cock with pleasure

Sissy POV - Sucking huge white cock with pleasure

XHamster 11 months ago

Miss Sally Pegs Her Fine Little Sissy

Miss Sally Pegs Her Fine Little Sissy

Amateur8 2 weeks ago

Brides Hands-free BBC Cumshots

Brides Hands-free BBC Cumshots

XHamster 4 months ago

Best femdom pegging porn compilation

Best femdom pegging porn compilation

AnySex 2 years ago

Sissy Stuffing Perverted Tasks for Feminization Gay Training

Sissy Stuffing Perverted Tasks for Feminization Gay Training

XHamster 3 weeks ago

Bi Femdom Blowjob POV, Two MILF Mouths One Cock, Bisexual Encouragement

65% HD 0:39 / 10:19

Bi Femdom Blowjob POV, Two MILF Mouths One Cock, Bisexual Encouragement

FapHouse 2 weeks ago

Tied Twink milked by Mistress with Ruined Cumshot

Tied Twink milked by Mistress with Ruined Cumshot

XHamster 1 year ago

Lipstick Sissy Clit: You'll Never be like Me. Femdom POV Sissy Training Feminization. Satin Panty Fetish Sissy Clit Worship. Red Lipstick Fetish

Lipstick Sissy Clit: You'll Never be like Me. Femdom POV Sissy Training Feminization. Satin Panty Fetish Sissy Clit Worship. Red Lipstick Fetish

StiefMutter 4 days ago

Sophia Loreen Party on Aug 24, 2026 - Part 3

53% 4K 2:00 / 59:20

Sophia Loreen Party on Aug 24, 2026 - Part 3

Camster 4 weeks ago

Anal Roleplay.

XHamster 3 weeks ago

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

TRANSSEXUAL Sissy Jism Hoe Extraordinary Face Pummel

TrannyGem 5 years ago

Ricck Smith Premiere Show

61% 4K 2:00 / 4:43

Ricck Smith Premiere Show

Flirt4Free 3 weeks ago

Christian & Nicco & Elvis Private Show

56% HD 2:00 / 11:48

Christian & Nicco & Elvis Private Show

Flirt4Free 2 years ago

The Gay Awakening Podcast Episode #26

75% HD 0:24 / 19:36

The Gay Awakening Podcast Episode #26

Clips4sale 3 years ago

Satin Sissy Training

Satin Sissy Training

StiefMutter 2 days ago

J.o.i. Stroke It, Jerk-off Instructions

68% 4K 2:00 / 2:09

J.o.i. Stroke It, Jerk-off Instructions

Flirt4Free 8 years ago

Cuck It Hard

Some.Porn 1 month ago

The Final Transformation Part 2

The Final Transformation Part 2

Dafreeporn 5 months ago

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

Sissy Slave Femdom Feminization Humiliation Nails Painted Chastity BDSM Real Homemade Amateur Milf

XHamster 2 years ago

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

Striptease, full nude, masturbation, tit play and ending with a deep blowjob - Part 2

Camster 2 years ago

Sissy Slut Worships My Strapon Sph Cum Countdown

Sissy Slut Worships My Strapon Sph Cum Countdown

FapHouse 1 week ago

Sissy Training Day 2. My Transformation Continues

Sissy Training Day 2. My Transformation Continues

XHamster 3 months ago

A Girl Is Going to Get Her Ass Fisted

A Girl Is Going to Get Her Ass Fisted

ShemaleSex 2 months ago

Chastity fag slave humiliation pet play bondage

Chastity fag slave humiliation pet play bondage

XHamster 8 months ago

Tatiana & Lord Private Show

Tatiana & Lord Private Show

Camster 3 weeks ago

Woman Milk Sissy Bi-atch in her FACEHOLE

Woman Milk Sissy Bi-atch in her FACEHOLE

TransTube.tv 1 year ago

Valexie Lux Private Show

Valexie Lux Private Show

Camster 1 month ago

Topped Toys Zeffir 130, still training to get it deep in me

Topped Toys Zeffir 130, still training to get it deep in me

XHamster 4 days ago

ANAL training for my DIAPER slave

ANAL training for my DIAPER slave

XHamster 2 years ago

Super Fuck Show

67% 4K 2:00 / 24:13

Super Fuck Show

Flirt4Free 1 year ago

Anal Training, Learning

Anal Training, Learning

XHamster 8 months ago

Bella Brookz Private Show

64% HD 2:00 / 9:02

Bella Brookz Private Show

Camster 3 years ago

The Gay Test: Swallow Your Roommate Load

40% HD 1:01 / 9:24

The Gay Test: Swallow Your Roommate Load

FapHouse 1 year ago

Custom Clip: You Become the Office Bitch

Custom Clip: You Become the Office Bitch

XHamster 2 years ago

Give up Your Life to Serve Me

HD 0:39 / 11:39

Give up Your Life to Serve Me

FapHouse 1 month ago

Heartless BBW Female-master Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piddle Drinking!

Heartless BBW Female-master Destroys Stepson CBT Boots, Deep Gagging, Anal Stretching, Sissification and Piddle Drinking!

PornFreeNow 2 months ago

HARD SPANKING AS SHE ANAL TRAINS ME

HARD SPANKING AS SHE ANAL TRAINS ME

XHamster 1 week ago

EARN THE COCK! Double bimbofication

Premium HD 13:26

EARN THE COCK! Double bimbofication

Clips4sale 1 week ago

Good Boy Takes Cock From Hot Dominatrix

60% HD 0:39 / 6:59

Good Boy Takes Cock From Hot Dominatrix

FapHouse 3 weeks ago

add me on snapchat-surfer.69

add me on snapchat-surfer.69

Eporner 7 years ago

Hard pegging compilation with lots of cum on chest

Hard pegging compilation with lots of cum on chest

SortPorn 3 years ago

My Sissy Sucks My Locked Husband… Who Thinks It’s Me - Mistress Julia

65% 1:01 / 12:15

My Sissy Sucks My Locked Husband… Who Thinks It’s Me - Mistress Julia

FapHouse 10 months ago

Blacked Big Ass Trans Samus Anal Creampie and Huge Cumfarts

Blacked Big Ass Trans Samus Anal Creampie and Huge Cumfarts

XHamster 8 months ago

Training makes perfect

Training makes perfect

XHamster 1 year ago

Humiliating Date Story by a Pathetic Piggy

59% HD 1:01 / 14:11

Humiliating Date Story by a Pathetic Piggy

FapHouse 11 months ago

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

51% HD 1:01 / 31:09

Cum Cow Training: Tgirl Bound, Cock Pumped, Milked & Ruined

FapHouse 5 months ago

Mdf: Valentin Gets His Prostate Milked Like a True Chaste-boy!

Mdf: Valentin Gets His Prostate Milked Like a True Chaste-boy!

XHamster 6 months ago

10 11 12 13 14

261,546 results found

Narrow your search

sissy anal training

Categories Pornstars

Parents

Pornhd.com uses the “Restricted To Adults” (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Pornhd.com. All rights reserved.

© 2026 Pornhd.com. All rights reserved.